Saint Petersburg Outdoor Activities

The founders of St. Petersburg probably didn't imagine future visitors rolling down its streets on upright, self-balancing machines. Mounted on Segway HTs, visitors on All About Fun Tours can do just that, cruising along the waterfront on devices that intuitively respond to their movements or fear of jellyfish. Tour options abound, and guides deliver a tutorial on Segway basics before leading groups around the historic city.

Located in the shadow of the Marriott hotel, Clearwater Jet Ski and Parasail outfits beachgoers with the equipment to safely speed across or sail above the waves. Its three-seater jet skis kick up massive wakes as they roar over the sapphire surface of the water, and tandem kayaks trundle along. Staff-operated speedboats tow parasails behind them, passengers getting a seagull’s view of the waves and a firm understanding of how silly the dog paddle looks from a distance.

The images of sharks and turtles swim across a 44-foot-tall mural created by Guy Harvey to welcome patrons into Surf Style's 55,000-square-foot shopping center, which the Tampa Bay Times called to “a baby Grand Central Station.” The artist's designs adorn an entire section of the center's racks of surf clothing, while other areas stock gear such as skateboards and skimboards.

Elsewhere, the sounds of crashing water and cheering bystanders lure shoppers to the FlowRider, a self-contained wave-pool machine that mimics some of Mother Nature's biggest waves. The machine incorporates aspects of surfing, snowboarding, and skateboarding and allows boarders to execute aerial maneuvers straight out of a pogo stick's wildest dreams. Visitors stow their cars in Surf Style’s six-level parking garage as they shop in the store or ride waves at nearby Clearwater Beach.

Certified as a 100 Ton Master Captain by the U.S. Coast Guard, Red Devil Fishing Adventures’ Captain John Gibson leads near-shore reef-fishing excursions in Gulf waters from Venice to Tarpon Springs. Captain John's 24-foot motorized vessel disengages its seaworthy hull from shore to chase after undersea denizens such as cobia, grouper, snapper, and mackerel, offering aspiring anglers high-quality gear and lines with which to angle. Besides fishing expeditions, the captain regularly wanders away from the mainland to engage in bird watching, shelling, nature tours, and languid afternoons of sunbathing on West Florida's isolated islands. Excursions run seven days a week and are subject to weather conditions, availability, and favorable predictions from the captain’s magic 8 ball.

The third annual St. Pete Oktoberfest, hosted by the Grand Central District Association, is St. Petersburg's largest beer festival, featuring craft-beer tastings and live music. Attendees can tipple samples from dozens of breweries, including Bell's Brewery, Dogfish Head, Sam Adams, Angry Orchard, and many others. A home brewer's challenge on Friday tests out homebrewed beers against old favorites, so home-beer enthusiasts can test out their recipes on actual people instead of the wild deer that show up in their backyards.

In addition to the extensive selection of microbrews and iconic beers, the two-day street festival also features live music, including performances from singer-songwriter John Kelly on Friday. Saturday's music merges rock, blues, jazz, and funk, with performances from Florida-native Damon Fowler, Bobby Lee Rodgers Trio, and Serotonic.

Sky Pirate Parasail's U.S. Coast Guard–licensed captains slip through John's Pass between Madeira Beach and Treasure Island while towing parasailers who glide under kaleidoscopic chutes tethered up to 1,200 feet in the air. After fastening their passengers, who range from school-aged kids to grandparents, into a secure harness, they fill the parachute's canopy with air and shuttle the skyward rider over the saltwater waves for an aerial jaunt. As the captain slackens the line and traces the coastline from offshore, the parasailer floats over the beach, the dolphins, and the gelatinous blob monster waving at sunbathers.